About City Bureau
City Bureau is an innovation lab reimagining local journalism, civic media, and participatory democracy. We equip people with civic skills, develop resources that directly meet people’s information needs, and create pathways for deliberative dialogue that strengthens communities. We envision a world where all communities have the information, tools, and resources they need to actively shape their futures and cultivate a more responsive and just democracy.
Location: Remote, with occasional travel to Chicago (City Bureau headquarters) and partner communities. If residence is in the Chicago area, will be expected to participate periodically in person at City Bureau community events.
ABOUT DOCUMENTERS
City Bureau’s Documenters program makes local democracy real and accessible to anyone. We do this by training and paying community members to attend and take notes at local public meetings, turning the knowledge, relationships, and capacity of local residents into a powerful community information resource.
Since launching Documenters in Chicago in 2016, local news and community organizations nationwide have adopted the program through the Documenters Network, which now includes more than 20 programs housed in local organizations across the country, with more added every year. Collectively, we have trained more than 4,000 community members and documented more than 5,000 public meetings across the country.
Using a network approach, City Bureau partners with local community and news organizations to start local Documenters programs (“sites”) in order to equip communities to understand and shape local policies and public systems. City Bureau stewards the overall Documenters program model; provides custom central technology through Documenters.org to operate and publish Documenters assignments; and offers convenings, template materials, and more to sites that support innovation, learning, and connection.
THE JOB: Senior Site Success Manager
City Bureau is seeking a Senior Site Success Manager to join our Documenters team and serve as a trusted partner, strategic advisor, and hands-on problem-solver for a portfolio of Documenters sites across the country. This is a senior-level role for someone who brings deep expertise in nonprofit revenue generation and development alongside a strong background in coaching and consulting; someone who thrives in complex multi-stakeholder environments and can lead difficult conversations with confidence and care.
You’ll manage a portfolio of up to six sites with a high degree of autonomy, owning relationships and outcomes across the full program lifecycle, from incubation and launch through growth, intervention, and, when necessary, offboarding. You’ll also contribute meaningfully to the broader strategy and systems that make the Documenters Network work at scale.
We’re looking for someone who combines the instincts of a skilled coach with the rigor of a strategic analyst - someone who can read a situation, identify what a site really needs, and design a path forward even when the terrain is complicated. The ideal candidate is comfortable leading organizational change conversations, synthesizing data into actionable insights, and contributing to team-wide learning and capacity building.
This role reports to the Director of Site Success and collaborates closely with cross-functional partners across product, communications, and operations.
You should apply if:
You are a skilled coach and relationship builder. You know how to build real trust with partners and how to have hard conversations without losing the relationship. You meet people where they are, adapt your approach to different leadership styles, and bring genuine investment to the success of the organizations you support.
You are a nonprofit revenue strategist and sustainability champion. You've helped organizations diversify their funding across grants, earned revenue, and institutional partnerships, and you know how to make that work feel accessible for teams that are stretched thin. You bring experience in the journalism or civic media funding landscape specifically, and you're energized by the challenge of helping small organizations build durable financial models.
You are a strategic problem-solver. You can look at a struggling partner, get curious about the root causes of what’s going wrong, and design a structured path toward improvement. You’re comfortable holding complexity, managing risk, and knowing when to escalate and when to act.
You want to shape the work, not just execute it. You’re energized by contributing to strategy and systems, not just working within them. You bring field insights to the table and help the team continuously improve how it supports sites at scale.
RESPONSIBILITIES
Site Portfolio Management & Success (50%)
Manage a portfolio of up to six Documenters sites with high autonomy, owning relationships and outcomes across the full program lifecycle: incubation, onboarding, launch, expansion, intervention, and off-boarding.
Serve as the primary decision-maker for day-to-day portfolio management, escalating high-risk or strategic decisions to the Director of Site Success.
Analyze and use qualitative and quantitative data across your portfolio, translating signals about site health, sustainability, and program quality into clear risk assessments and recommended actions.
Identify risk, design plans to mitigate that risk, and lead interventions to support sites through leadership transitions, funding instability, and performance challenges.
Manage a subset of Documenter lifecycle workflows, taking primary responsibility for improvement, learning, adoption, and innovation in those areas.
Program & Site Sustainability/Revenue Strategy (40%)
Serve as a thought partner and collaborator to the Director and other Site Success Managers on program strategy, surfacing insights from the field and your experience and informing new or differentiated approaches to how City Bureau supports sites.
Drive the operational execution of the Site Leadership strategy in partnership with the Director of Site Success, including facilitating working groups focused on revenue generation, developing resources to support site sustainability, and directly supporting sites in identifying and pursuing funding diversification strategies.
Identify systemic issues affecting multiple sites and propose coordinated solutions in partnership with the broader team.
Team Systems & Capacity Building (10%)
Contribute to internal training and capacity building for the Site Success team, modeling advanced coaching and consulting behaviors and providing peer mentorship.
Contribute to team design conversations by surfacing workload trends, capacity gaps, and process improvement opportunities.
Manage complex cross-team coordination to ensure site needs inform roadmap and resource priorities across product, communications, and operations.
Note: After one year, this role may evolve to directly manage our team of three (3) Site Success Managers. This decision will be made with input from the Senior Site Success Manager, Site Success Managers, and in alignment with our overarching team, department, and organizational goals.
QUALIFICATIONS
Partnership & Portfolio Management
5+ years of experience managing complex, multi-stakeholder partnerships or program portfolios with a high degree of autonomy.
Demonstrated experience supporting organizations through change, including leadership transitions, funding instability, and performance improvement.
Familiarity with program lifecycle management: incubation, launch, growth, intervention, and offboarding.
Coaching & Consulting
Background in coaching, consulting, or technical assistance, ideally in a network or multi-site context.
Demonstrated ability to lead difficult conversations with clarity, directness, and care.
Strong and effective approach to managing toward results with an equity and coaching lens.
Sector Knowledge and Experience
Experience working with or within journalism, civic media, nonprofit, or community-based organizations; direct experience with the Documenters network is a strong plus.
Experience with nonprofit fundraising and revenue generation models, including diversified funding strategies, grant funding, and earned revenue, for local journalism, civic engagement, or adjacent fields is highly valued.
Data & Strategic Analysis
Comfort with data analysis and translating qualitative and quantitative signals into clear narratives, risk flags, and strategic recommendations.
Experience maintaining systems and dashboards to track organizational health and program quality.
Cross-Functional Collaboration
Cross-functional project management experience, particularly coordinating across product, communications, and program teams.
Proactive communicator with high follow-through and strong written communication skills.
COMPENSATION, BENEFITS AND SUPPORT
$80,000 annual salary. City Bureau uses a universal compensation system.
Full-time with a benefits package including health care, dental, vision, and life insurance.
Employer-sponsored 401k with 100% employer match up to 2% of salary.
$1,000 combined annual technology and work tools and professional development allowance.
15 days paid vacation, not including health days.
11 company holidays each year, which may be exchanged for employees who celebrate other holidays.
A 4.5-day week for most of the year; during three summer months, City Bureau operates on a 4-day work week.
Remote, with occasional travel to Chicago and partner communities; Chicago-area staff are expected to participate periodically in in-person City Bureau community events.
A culture of intentional professional development and organizational learning.
OUR TIMELINE
We’re projecting the following timeline for this hiring process. We will notify candidates of any shifts as we move through the process.
Application closes on Thursday, April 16, 2026
Within two weeks of closing applications, you will know if you’ve moved onto the interview stage
Within two weeks of your interview, you’ll know if you moved onto the case exercise stage
Within two weeks of your case exercise completion, you’ll know if you moved onto the final interview
We expect to make a final offer by late May.
City Bureau is an equal opportunity employer committed to creating an inclusive environment for all employees.